School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, PR China.
Org Lett. 2012 Jan 6;14(1):390-3. doi: 10.1021/ol203154j. Epub 2011 Dec 20.
The Pd-catalyzed Suzuki-Miyaura coupling reaction of unsymmetric 1,3-disubstituted secondary allylic carbonates with arylboronic acids has been developed in a wet solvent under a base-free system to afford allyl-aryl coupling products in a high level of isolated yields with complete regio- and E/Z-selectivities with good to excellent chemoselectivities. The coupling reaction of optically active allyl carbonates gave allyl-aryl coupling products with excellent enantioselectivities with inversion of the stereochemistry. This coupling method was successfully applied to the synthesis of (S)-naproxen.
钯催化的非对称 1,3-二取代烯丙基碳酸酯与芳基硼酸的铃木-宫浦偶联反应在无碱的湿溶剂体系中得到发展，以高产率、完全区域和 E/Z 选择性以及良好到优秀的化学选择性得到烯丙基-芳基偶联产物。光学活性烯丙基碳酸酯的偶联反应得到了具有优异对映选择性的烯丙基-芳基偶联产物，立体化学发生了反转。该偶联方法成功应用于 (S)-萘普生的合成。
